I think you are over-estimating the impact of a "top 5" master's program vs an average master's program. I had a very similar trajectory to you and went to an average master's program.
The major difference between you and me is that I never wanted to work for a Google, Amazon, or Hedge Fund and wanted to work at smaller companies. Salary suffered because of my reluctance to even compete for those jobs.
> The biggest boost in my career earnings came when I transitioned from a Computer Hardware engineer to a Software Engineer
I also disagree with this. The biggest boost in your career earnings came from working at (1) financial companies and (2) working at FAANG. I don't think you have enough data to say that your area of focus is what to lead to this, and I personally think it is wrong. Maybe it opened doors for you however